Hydrochloric Acid → 2-Chloro-9-cyclohexyl-5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-one

HRID 2111305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111305
C([O:5][C:6](=O)[CH2:7][CH2:8][N:9]([C:16]1[C:21]([N+:22]([O-])=O)=[CH:20][N:19]=[C:18]([Cl:25])[N:17]=1)[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(C)(C)C.C(O)C.Cl>C(OCC)(=O)C.O>[Cl:25][C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:6](=[O:5])[CH2:7][CH2:8][N:9]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:16]=2[N:17]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 866234063-[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclohexyl-amino]-propionic acid tert-butyl ester

Produkt 1

HCID 866175922-Chloro-9-cyclohexyl-5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-oneAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1.53 g (0.004 mole) of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclohexyl-amino]-propionic acid tert-butyl ester (IV-20) in 20 mL of ethyl acetate was added in portions over 10 minutes to a mixture of 2.69 g (0.012 mole) of stannous chloride dihydrate, 12 mL of ethanol and 0.5 mL of hydrochloric acid. The mixture was stirred overnight and then diluted with 30 mL of water and extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (100:0-92:8) to give 0.47 g of 2-chloro-9-cyclohexyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-20).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with dichloromethane-methanol (100:0-92:8)

Quellen und Nachweise

ORD-Eintrag
ord-278512b9d9664f3d8a820781f3b30f0c
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517873B2

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